[CH2:1]([Li])[CH3:2].[CH3:4][C:5]([CH:10]=[CH:11][CH2:12][CH:13]([CH3:21])[CH2:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][C:7]([OH:9])=O.[Cl-].[NH4+]>C1C=CC=CC=1.CCOCC>[CH3:4][C:5]([CH:10]=[CH:11][CH2:12][CH:13]([CH3:21])[CH2:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][C:7](=[O:9])[CH2:1][CH3:2]To a stirred solution of 9.5 ml. of a one molar solution of ethyllithium in benzene and 50 ml ether, under nitrogen is added at 0° 1.0 g. of 3,7,11,11-tetramethyldodeca-2,4-dienoic acid in 10 ml. ether. The reaction mixture is stirred for three hours and then is poured into a rapidly stirred saturated aqueous ammonium chloride solution followed by the addition of 50 ml. of ether. The organic layer is separated and then is washed with saturated sodium chloride. The solution is dried over magnesium sulfate and the solvent is removed to yield 5,9,13,13-tetramethyltetradeca-4,6-dien-3-one.
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